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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Ashland vacation rentals

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is CA $157
CA $354 total
includes taxes & fees
Oct 28 - Oct 29
Barclay Klum House by WanderLodges
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

2. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Excellent stay. Very responsive host. Would come back"
United States
Scott N.
The price is CA $233
CA $426 total
includes taxes & fees
Nov 24 - Nov 25
Courtside Cottage - WalkScore 93 - Dog Friendly
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

3. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is CA $144
CA $268 total
includes taxes & fees
Nov 9 - Nov 10
Hanna's House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

4. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is CA $241
CA $471 total
includes taxes & fees
Nov 1 - Nov 2
The Mountain Ave House by WanderLodges
A house with a wooden deck, a stone wall, and a wooden fence.

5. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is CA $234
CA $400 total
includes taxes & fees
Nov 1 - Nov 2
The Ashland Cottage, walk to town
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

6. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is CA $224
CA $482 total
includes taxes & fees
Oct 28 - Oct 29
Savage Upon Siskiyou
A deck with a fire pit, outdoor seating, and a view of the countryside.

7. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is CA $256
CA $543 total
includes taxes & fees
Nov 1 - Nov 2
Grandview of Ashland
A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

8. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is CA $175
CA $328 total
includes taxes & fees
Oct 29 - Oct 30
Charming carriage house in Ashland near downtown
A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

9. The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
9.8 out of 10, Exceptional, (29 reviews)
"A great place to call home while you're away from home."
United States
Tara M.
The price is CA $126
CA $298 total
includes taxes & fees
Oct 28 - Oct 29
The Ashland Social | Guest Studio
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

10. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (55 reviews)
"The bungalow was great. Every room was comfortable and efficient for what we needed. The location is perfect...quiet yet easy walk to anywhere downtown. We would stay here again!!"
United States
Amy R.
The price is CA $131
CA $294 total
includes taxes & fees
Nov 2 - Nov 3
East Main Downtown Bungalow
A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

11. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.6 out of 10, Exceptional, (24 reviews)
"Just a little cleaner exterior"
United States
David
The price is CA $221
CA $311 total
includes taxes & fees
Oct 28 - Oct 29
Chateau Herbe ~ Oberon Suite w/ Kitchen
A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

12. Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (61 reviews)
"This is an excellent place to stay. It is well equipped with everything you might need for your stay. And the location is perfect."
United States
Karen G.
The price is CA $165
CA $297 total
includes taxes & fees
Nov 11 - Nov 12
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
A two-story house with a porch, a wooden fence, and a paved driveway.

13. Downtown Ashland Studio - 3 blocks from the plaza!

Downtown Ashland Studio - 3 blocks from the plaza!
Ashland
9.2 out of 10, Wonderful, (24 reviews)
"This was a great little place in a great location. The host was very responsive, really easy to work with and made our stay easy. We highly recommend!"
United States
Santiago L.
The price is CA $133
CA $306 total
includes taxes & fees
Oct 28 - Oct 29
Downtown Ashland Studio - 3 blocks from the plaza!
A living room with a green sofa, a television, a wooden coffee table, and a patterned rug.

14. The Matriarch| Suite 3 | Pet friendly

The Matriarch| Suite 3 | Pet friendly
Historic Railroad District
9.6 out of 10, Exceptional, (8 reviews)
"We stayed one night and walked easily to a show in one of the Shakespeare theatres. The apartment was super-comfortable and excellent in every way! Highly recommended!"
United States
Daniel
The price is CA $179
CA $231 total
includes taxes & fees
Oct 28 - Oct 29
The Matriarch| Suite 3 | Pet friendly
A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

15. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Historic Downtown District
9.8 out of 10, Exceptional, (137 reviews)
"Room was in fantastic shape, clean, well decorated, close to everything. As an Air B&B owner, I recommend, if staying Ashland stay here. Great host."
United States
James C.
The price is CA $176
CA $364 total
includes taxes & fees
Nov 1 - Nov 2
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
A porch with wicker furniture, a small table, and a plaid rug.

16. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location- We typically visit twice a year and like to stay in railroad district as it is close to restaurants and OSF. Highly recommend Swank House."
United States
Sue K.
The price is CA $172
CA $223 total
includes taxes & fees
Oct 28 - Oct 29
Affordable Luxury- One block to Downtown
A two-story wooden house with a fenced backyard, outdoor seating, and a statue.

17. The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District

The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District
Historic Railroad District
The price is CA $122
CA $247 total
includes taxes & fees
Oct 28 - Oct 29
The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District
A two-story building with a balcony, a patio with white chairs, and a statue.

18. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"The sights stunning, the garden a delight & the jacuzzi soak enriched my soul & ailing body"
United States
David B.
The price is CA $137
CA $265 total
includes taxes & fees
Oct 28 - Oct 29
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Comfortable wicker seating to enjoy your morning coffee or evening wine.

19. Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!

Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location and had all the touches to make it a comfortable stay"
United States
Sara C.
The price is CA $193
CA $367 total
includes taxes & fees
Oct 28 - Oct 29
Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
A modern bedroom with a large bed, wooden slatted ceiling, a flat-screen TV, and a built-in wardrobe.

20. Swank House -Downtown Suite- Pet Friendly

Swank House -Downtown Suite- Pet Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, cute and private outdoor patio. Cozy but spacious bed and room. Pet-Friendly. Would definitely stay again."
United States
Katie I.
The price is CA $155
CA $209 total
includes taxes & fees
Nov 2 - Nov 3
Swank House -Downtown Suite- Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Ashland Springs Hotel

Ashland Springs Hotel

8/10 Good
"One of the nicer hotels in Ashland. Very comfortable bed and pillows! Condition could use some work - a bit worn here and there and the carpets could use an upgrade. Staff were nice, breakfast was good. Location can't be beat."
Carol 1-night trip
Posted 13 hours ago
Ashland Springs Hotel

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theater scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Premier Downstairs Flat in Perfect Down Town Location : This highly rated vacation home rental in Ashland is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. .

How many vacation rentals are there in Ashland?

Choose from 106 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Oregon Cabaret Theatre are other places to visit while you're in town.

What are vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.